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{{Chembox
{{Orphan|date=June 2023}}
| ImageFile = Periplocin.svg
| ImageSize = 200px
| IUPACName = 3-[(3''S'',5''S'',8''R'',9''S'',10''R'',13''R'',14''S'',17''R'')-5,14-dihydroxy-3-[(2''R'',4''S'',5''R'',6''R'')-4-methoxy-6-methyl-5-[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
|Section1={{Chembox Identifiers
| CASNo = 13137-64-9
| CASNo_Ref = {{Cascite|changed|CAS}}
| ChemSpiderID = 16739442
| EC_number = 683-188-2
| PubChem = 14463159
| UNII = 199X940O3K
| StdInChI=1S/C36H56O13/c1-18-31(49-32-30(41)29(40)28(39)25(16-37)48-32)24(44-4)14-27(46-18)47-20-5-9-33(2)22-6-10-34(3)21(19-13-26(38)45-17-19)8-12-36(34,43)23(22)7-11-35(33,42)15-20/h13,18,20-25,27-32,37,39-43H,5-12,14-17H2,1-4H3/t18-,20+,21-,22+,23-,24+,25-,27+,28-,29+,30-,31-,32+,33-,34-,35+,36+/m1/s1
| StdInChIKey = KWBPKUMWVXUSCA-AXQDKOMKSA-N
| SMILES = C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
}}
|Section2={{Chembox Properties
| C=36|H=56|O=13
}}
|Section7={{Chembox Hazards
| GHS_ref=<ref>{{cite web |title=Periplocin |url=https://pubchem.ncbi.nlm.nih.gov/compound/14463159#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| GHSPictograms = {{GHS06}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|300|330|373}}
| PPhrases = {{P-phrases|260|264|270|271|284|301+316|304+340|316|319|320|321|330|403+233|405|501}}
}}
|Section8={{Chembox Related
}}
}}


'''Periplocin''' is a plant-derived [[glycoside]] whereby the sugar moiety is linked to a [[steroid]]. It can be extracted from cortex periplocae (CPP), the dry root of ''[[Periploca (plant)|Periploca]] sepium''.<ref name=liy>{{cite journal |doi=10.3390/molecules21121702 |doi-access=free |title=A Review on Phytochemistry and Pharmacology of Cortex Periplocae |year=2016 |last1=Li |first1=Yang |last2=Li |first2=Jin |last3=Zhou |first3=Kun |last4=He |first4=Jun |last5=Cao |first5=Jun |last6=An |first6=Mingrui |last7=Chang |first7=Yan-Xu |journal=Molecules |volume=21 |issue=12 |page=1702 |pmid=27973416 |pmc=6272874 }}</ref><ref name=guo>{{cite journal |doi=10.1016/j.jep.2013.03.036 |title=Antagonism of Cortex Periplocae extract-induced catecholamines secretion by Panax notoginseng saponins in cultured bovine adrenal medullary cells by drug combinations |year=2013 |last1=Guo |first1=Hao |last2=Mao |first2=Haoping |last3=Pan |first3=Guixiang |last4=Zhang |first4=Han |last5=Fan |first5=Ganwei |last6=Li |first6=Weiwei |last7=Zhou |first7=Kun |last8=Zhu |first8=Yan |last9=Yanagihara |first9=Nobuyuki |last10=Gao |first10=Xiumei |journal=Journal of Ethnopharmacology |volume=147 |issue=2 |pages=447–455 |pmid=23524165 }}</ref>
'''Periplocin''' is a plant-derived [[glycoside]] whereby the sugar moiety is linked to a [[steroid]]. It can be extracted from cortex periplocae (CPP), the dry root of [[Periploca (plant)|Periploca]] sepium.<ref name=liy>{{cite journal| url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272874/|
authors=Li Y, Li J, Zhou K, He J, Cao J, An M, Chang YX.|title= A Review on Phytochemistry and Pharmacology of Cortex Periplocae.| journal= Molecules. 2016 Dec 10;21(12):1702.|doi=10.3390/molecules21121702
| pmid=27973416 }}</ref><ref name=guo>{{cite journal| url=https://www.sciencedirect.com/science/article/abs/pii/S037887411300192X?via%3Dihub | author=Guo H, Mao H, Pan G, Zhang H, Fan G, Li W, Zhou K, Zhu Y, Yanagihara N, Gao X| title=Antagonism of Cortex Periplocae extract-induced catecholamines secretion by Panax notoginseng saponins in cultured bovine adrenal medullary cells by drug combinations.| journal=J Ethnopharmacol. 2013; 147(2):447-55| doi=10.1016/j.jep.2013.03.036|pmid=23524165}}</ref>


CPP's healing activities have long been recognized in [[traditional Chinese medicine]]<ref name=guo/> where it has been used to treat [[rheumatoid arthritis]].<ref name=liy/> Scientific investigations have identified over 100 components of which periplocin has been a major focus both for its toxicity as well as for its potential beneficial pharmaceutical effects.<ref name=liy/> Besides the cardiac glycosides with periplocin as its main constituent, the CPP contains different C21-steroidal glycosides such as periplocodides and [[pregnene]] derivatives, [[fatty acid]]s, [[volatile oil]]s, [[terpene]]s, and others.<ref name=liy/>
CPP's healing activities have long been recognized in [[traditional Chinese medicine]]<ref name=guo/> where it has been used to treat [[rheumatoid arthritis]].<ref name=liy/> Scientific studies of CPP have identified over 100 components of which periplocin has been a major focus both for its toxicity as well as for its potential beneficial pharmaceutical effects.<ref name=liy/> Besides the cardiac glycosides with periplocin as its main constituent, the CPP contains different C21-steroidal glycosides such as periplocodides and [[pregnene]] derivatives, [[fatty acid]]s, [[volatile oil]]s, [[terpene]]s, and others.<ref name=liy/>


Higher doses of periplocin are toxic as a [[cardiac glycoside]].<ref>{{cite journal |doi=10.1002/jssc.202001262 |title=Metabolomics study on the periplocin-induced cardiotoxicity and the compatibility of periplocin and Panax notoginseng saponins in reducing cardiotoxicity in rats by GC-MS |year=2021 |last1=Wang |first1=Wei |last2=Fan |first2=Yuqi |last3=Huang |first3=Xuhua |last4=Li |first4=Li |last5=Wang |first5=Songrui |last6=Xue |first6=Zixiang |last7=Ouyang |first7=Huizi |last8=He |first8=Jun |journal=Journal of Separation Science |volume=44 |issue=14 |pages=2785–2797 |pmid=33961332 |s2cid=233985785 }}</ref>
Higher doses of periplocin are toxic as a cardiac glycoside.<ref>{{cite journal |url=https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/abs/10.1002/jssc.202001262| authors=
Wang, W., Fan, Y., Huang, X., Li, L., Wang, S., Xue, Z., Ouyang, H., & He, J. (2021).|title= Metabolomics study on the periplocin-induced cardiotoxicity and the compatibility of periplocin and Panax notoginseng saponins in reducing cardiotoxicity in rats by GC-MS. |journal=Journal of Separation Science, 44(14), 2785-2797.| doi=10.1002/jssc.202001262|pmid=33961332}}</ref>


Potential medical applications of periplocin are focused on these areas:<ref name=liy/>
Potential medical applications of periplocin are focused on these areas:<ref name=liy/>
Line 15: Line 39:
* Cardiotonic activity. Traditional use includes an application for heart failure. Structure and function of cardiac muscle were improved in rats.
* Cardiotonic activity. Traditional use includes an application for heart failure. Structure and function of cardiac muscle were improved in rats.


Periplocin's metabolites, periplocymarin and periplogenin,<ref>{{cite journal |url=https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/bmc.5283| authors=Wang, S., Yu, X., Wu, S., Yang, W., Gao, Y., Wang, W. H., Wang, Q., Wei, M., Zhu, M., Wu, J., Yuan, Z., & Li, Y.| title=Simultaneous determination of periplocin, periplocymarin, periplogenin, periplocoside M and periplocoside N of Cortex Periplocae in rat plasma and its application to a pharmacokinetic study. |journal=Biomedical Chromatography. |doi=10.1002/bmc.5283 |pmid=34816469}}</ref> have also shown some pharmacological effects.
Periplocin's metabolites, periplocymarin and periplogenin,<ref>{{cite journal |doi=10.1002/bmc.5283 |title=Simultaneous determination of periplocin, periplocymarin, periplogenin, periplocoside M and periplocoside N of Cortex Periplocae in rat plasma and its application to a pharmacokinetic study |year=2022 |last1=Wang |first1=Shuyao |last2=Yu |first2=Xin |last3=Wu |first3=Siyang |last4=Yang |first4=Wei |last5=Gao |first5=Yang |last6=Wang |first6=Weihua |last7=Wang |first7=Qiutao |last8=Wei |first8=Mengmeng |last9=Zhu |first9=Mingying |last10=Wu |first10=Jiarui |last11=Yuan |first11=Zheng |last12=Li |first12=Yingfei |journal=Biomedical Chromatography |volume=36 |issue=3 |pages=e5283 |pmid=34816469 |s2cid=244529941 }}</ref> have also shown some pharmacological effects.


Potential [[senolytics|senolytic activity]] was suggested by an [[artificial intelligence|AI]] structural analysis of over 4,000 chemicals in 2013.<ref>{{cite web |url=https://www.openaccessgovernment.org/ai-anti-aging-research-drugs-malfunctioning-cells/161082/ |author=NN | title=AI and anti-aging research: Unveiling the latest drug discovery| publisher=Open Access Government |date=June 15, 2023}}</ref>
==References==
==References==
{{Reflist}}
{{Reflist}}
Line 22: Line 47:
[[Category:Plant toxins]]
[[Category:Plant toxins]]
[[Category:Cardiac glycosides]]
[[Category:Cardiac glycosides]]
[[Category:Steroids]]

Latest revision as of 07:56, 7 February 2024

Periplocin
Names
IUPAC name
3-[(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.208.699 Edit this at Wikidata
EC Number
  • 683-188-2
UNII
  • InChI=1S/C36H56O13/c1-18-31(49-32-30(41)29(40)28(39)25(16-37)48-32)24(44-4)14-27(46-18)47-20-5-9-33(2)22-6-10-34(3)21(19-13-26(38)45-17-19)8-12-36(34,43)23(22)7-11-35(33,42)15-20/h13,18,20-25,27-32,37,39-43H,5-12,14-17H2,1-4H3/t18-,20+,21-,22+,23-,24+,25-,27+,28-,29+,30-,31-,32+,33-,34-,35+,36+/m1/s1
    Key: KWBPKUMWVXUSCA-AXQDKOMKSA-N
  • C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
Properties
C36H56O13
Molar mass 696.831 g·mol−1
Hazards
GHS labelling:[1]
GHS06: ToxicGHS08: Health hazard
Danger
H300, H330, H373
P260, P264, P270, P271, P284, P301+P316, P304+P340, P316, P319, P320, P321, P330, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Periplocin is a plant-derived glycoside whereby the sugar moiety is linked to a steroid. It can be extracted from cortex periplocae (CPP), the dry root of Periploca sepium.[2][3]

CPP's healing activities have long been recognized in traditional Chinese medicine[3] where it has been used to treat rheumatoid arthritis.[2] Scientific studies of CPP have identified over 100 components of which periplocin has been a major focus both for its toxicity as well as for its potential beneficial pharmaceutical effects.[2] Besides the cardiac glycosides with periplocin as its main constituent, the CPP contains different C21-steroidal glycosides such as periplocodides and pregnene derivatives, fatty acids, volatile oils, terpenes, and others.[2]

Higher doses of periplocin are toxic as a cardiac glycoside.[4]

Potential medical applications of periplocin are focused on these areas:[2]

  • Anti-inflammatory effects. Periplocin and its derivatives have shown anti-inflammatory effects.
  • Antitumor activity. A number of in vivo and in vitro studies suggest that periplocin inhibits tumor growth. Studies show both inhibition of growth as well as induction of apoptosis.
  • Cardiotonic activity. Traditional use includes an application for heart failure. Structure and function of cardiac muscle were improved in rats.

Periplocin's metabolites, periplocymarin and periplogenin,[5] have also shown some pharmacological effects.

Potential senolytic activity was suggested by an AI structural analysis of over 4,000 chemicals in 2013.[6]

References

[edit]
  1. ^ "Periplocin". pubchem.ncbi.nlm.nih.gov.
  2. ^ a b c d e Li, Yang; Li, Jin; Zhou, Kun; He, Jun; Cao, Jun; An, Mingrui; Chang, Yan-Xu (2016). "A Review on Phytochemistry and Pharmacology of Cortex Periplocae". Molecules. 21 (12): 1702. doi:10.3390/molecules21121702. PMC 6272874. PMID 27973416.
  3. ^ a b Guo, Hao; Mao, Haoping; Pan, Guixiang; Zhang, Han; Fan, Ganwei; Li, Weiwei; Zhou, Kun; Zhu, Yan; Yanagihara, Nobuyuki; Gao, Xiumei (2013). "Antagonism of Cortex Periplocae extract-induced catecholamines secretion by Panax notoginseng saponins in cultured bovine adrenal medullary cells by drug combinations". Journal of Ethnopharmacology. 147 (2): 447–455. doi:10.1016/j.jep.2013.03.036. PMID 23524165.
  4. ^ Wang, Wei; Fan, Yuqi; Huang, Xuhua; Li, Li; Wang, Songrui; Xue, Zixiang; Ouyang, Huizi; He, Jun (2021). "Metabolomics study on the periplocin-induced cardiotoxicity and the compatibility of periplocin and Panax notoginseng saponins in reducing cardiotoxicity in rats by GC-MS". Journal of Separation Science. 44 (14): 2785–2797. doi:10.1002/jssc.202001262. PMID 33961332. S2CID 233985785.
  5. ^ Wang, Shuyao; Yu, Xin; Wu, Siyang; Yang, Wei; Gao, Yang; Wang, Weihua; Wang, Qiutao; Wei, Mengmeng; Zhu, Mingying; Wu, Jiarui; Yuan, Zheng; Li, Yingfei (2022). "Simultaneous determination of periplocin, periplocymarin, periplogenin, periplocoside M and periplocoside N of Cortex Periplocae in rat plasma and its application to a pharmacokinetic study". Biomedical Chromatography. 36 (3): e5283. doi:10.1002/bmc.5283. PMID 34816469. S2CID 244529941.
  6. ^ NN (June 15, 2023). "AI and anti-aging research: Unveiling the latest drug discovery". Open Access Government.
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